My boyfriend and I have been together for a year now and have an extremely trusting relationship. We have tried anal sex a few times and always with the same result. It does feel good, kind of, but can be quite uncomfortable for me too. The best way to explain it is that it feels exactly like I’m having a bowel movement and bowel movements aren’t particularly pleasurable to me. I expected it to feel not only different but better. We have tried a couple of positions including doggy-style with my back straight and me on my back with legs on his shoulders and him leaning over me a bit. We always use a water-based lube. I really want to enjoy anal, so is there any advice you can give us to help make it more pleasurable?

–Anal Vixen Wannabe

Since it’s difficult to determine exactly what people mean sometimes, I want to acknowledge that you said your bowel movements aren’t “particularly pleasurable”; if you are having a lot of discomfort, you should see a doctor. If you meant that pooping doesn’t get you off, then here are my thoughts. Lots of anal novices say that the first few times they get fucked in the ass, it feels like they have to go to the bathroom. It makes sense, because all the nerve endings are being stimulated, and another activity where we experience that is a bowel movement. Usually, after the first few times, this sensation (or at least the urgent feeling to run to the toilet) subsides. You may prefer the stimulation of a butt plug, which goes in and stays in, to a lot of in-and-out fucking.

Though I think it could be your brain that’s tripping you up on this one, and you could be stuck on your association with butt sex and defecation. There are several elements of anal sex that are a lot different than going to the john, namely the addition of sexual sensations like vaginal and clitoral stimulation and a hot, horny guy you love and trust. Right now, it seems like you feel a sensation and automatically associate it with a non-sexual activity, and you cannot get past that. Some solo sessions where you experiment with different toys and different sensations may help you find the things that work best for you and get you reacquainted with your ass in a new way. If you can “retrain” your brain to eroticize your ass as the erogenous zone that it is, you may find yourself more open to feeling pleasure there.